Electrochemical Oxidation of 2, 6-Di-tert-butyl-4-methylphenol in Basic Methanol

Abstract

Electrochemical oxidation of 2, 6-di-tert-butyl-4-methylphenol (1) in methanol containing sodium methoxide gave side-chain-oxidized phenols, ArCH₂OMe, ArCHO, and ArCOOMe (Ar=3, 5-di-tert-butyl-4-hydroxyphenyl), together with 2, 6-di-tert-butylbenzoquinone and 3, 5, 3', 5'-tetra-tert-butyl-4, 4'-diphenoquinone. The product distribution varied with the electricity consumption. Based on the results obtained, a simple electrochemical transformation of 1 to the hydroxybenzaldehyde ArCHO was effected.